Lawesson's reagent → HCID 15485216, compound

HRID 1586462Notes

Reaction equation

HRID 1586462 reaction equation
[CH2:1]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][NH:13][C:14]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:25][CH2:26][CH3:27])[N:17]=2)=O)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:37])=CC=1>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[CH2:1]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][NH:13][C:14]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:25][CH2:26][CH3:27])[N:17]=2)=[S:37])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 87949Lawesson's reagentHCID 15435289HCID 15435289, compound

Product 1

HCID 15485216HCID 15485216, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

To a solution of N-[2-(4-n-butyl-1-piperazinyl)-ethyl]-1-n-propylindazole-3-carboxamide (0.39 g) obtained in Example 3 in toluene (10 ml) was added Lawesson reagent (0.64 g) at room temperature, and the mixture was heated under reflux for one hour. The reaction solution was cooled to room temperature, diluted with chloroform (50 ml), and then washed with saturated aqueous sodium hydrogencarbonate (50 ml). The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by thin-layer chromatography on silica gel (chloroform:methanol:aqueous ammonia=8:2:0.2) to give the title compound (0.36 g) as a pale yello; oily substance. Yield=88%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for one hour
  3. washwashed with saturated aqueous sodium hydrogencarbonate (50 ml)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by thin-layer chromatography on silica gel (chloroform:methanol:aqueous ammonia=8:2:0.2)

Sources & evidence

ORD record
ord-3f581e3c17734df6a457b9c62c921f34
Source dataset
uspto-grants-1999_08
Patent number
US05945434

Reaction notes

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